Acetaldehyde → 2,8-Dimethyl-1-oxa-3,8-diazaspiro[4.5]decane

HRID 1187317Notes

Reaction equation

[NH2:1][CH2:2][C:3]1([OH:10])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=O.[Mg+2].[CH:17](=O)[CH3:18]>ClCCl>[CH3:17][CH:18]1[NH:1][CH2:2][C:3]2([CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]2)[O:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-aminomethyl-1-methyl-piperidin-4-ol (2.127 g, 14.77 mmol) in dichloromethane (15 ml) was added anhydrous magnesium sulfate (2.9 g). The resulting mixture was cooled to 0° C. and freshly distilled acetaldehyde (835 μl, 14.78 mmol) was added. After 6 h of stirring at room temperature, the mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound (2.16 g) as an almost colorless liquid. 1H NMR (CDCl3, 500 MHz) δ 4.60 (q, J=5.40 Hz, 1H, CHCH3), 3.01 (d, J=12 Hz, 1H, CHHNH), 2.76 (d, J=12 Hz, 11-1, CHHNH), 2.55-2.31 (m, 4H, CH2N), 2.28 (s, 3H, NCH3), 1.77-1.58 (m, 4H, CH2CO), 1.36 (d, J=5.40 Hz, 3H, CH3CH) ppm; 13C NMR (CDCl3, 300 MHz) δ 87.57 (CH), 57.19 (CH2), 53.14 (C), 52.96 (CH2), 46.15 (CH3), 37.28 (CH2), 35.73 (CH2), 20.32 (CH3) ppm.

Workup

filtrationthe mixture was filtered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b3e07410df6d464fb749c7447ffb0b8f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673931B2

Reaction notes

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